Related Experiment Video
Updated: Jan 8, 2026
![Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F2755.jpg&w=3840&q=50)
08:33
Microwave-assisted One-pot Synthesis of N-succinimidyl-4-[18F]fluorobenzoate [18F]SFB
Published on: June 28, 2011
13.3K
Fluorothiazynes as SuFEx Ambiphiles: Interconversion to Amino-sulfurdiimidoyl Fluorides
Kexin Su1,2, Luc Van Meervelt1, Steven H L Verhelst3
1Department of Chemistry, Sustainable Chemistry for Metals and Molecules (SCM2), KU Leuven, Celestijnenlaan 200F box 2404, Leuven, 3001, Belgium.
Angewandte Chemie (International Ed. in English)
|December 12, 2025
Summary
Researchers developed a new method to synthesize aminosulfurdiimidoyl fluorides (ASDFs) from amino difluorothiazynes. This discovery offers a versatile platform for creating novel sulfur(VI) compounds for medicinal chemistry applications.
Area of Science:
- Medicinal Chemistry
- Organic Synthesis
- Sulfur Chemistry
Background:
- Sulfur(VI) functional groups are crucial in drug design, but complex cores are underexplored.
- Existing scaffolds primarily use sulfonamides, sulfones, and sulfates.
Purpose of the Study:
- To establish a general synthetic route to aminosulfurdiimidoyl fluorides (ASDFs).
- To explore the chemical reactivity and potential of ASDFs as building blocks.
Main Methods:
- Sequential alkylation and imination of amino difluorothiazynes.
- Utilizing the ambiphilic nature of fluorothiazynes to form thiazynium intermediates.
- Trapping intermediates with primary amides to yield ASDFs.
Main Results:
- A novel, general route to ASDFs was established from amino difluorothiazynes.
- ASDFs were synthesized in good yields and demonstrated reactivity as SuFEx electrophiles.
- An unsymmetrically substituted tetraimidosulfur species was generated, a likely first.
Conclusions:
- Introduced the first general synthetic pathway to aminosulfurdiimidoyl fluorides (ASDFs).
- ASDFs represent stable, functionally diverse platforms for chemical diversification in medicinal chemistry.
- Expanded the scope of azasulfur(VI) fluoride chemistry.
More Related Videos
Related Concept Videos
01:13Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
7.3K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
7.3K
02:26Preparation and Reactions of Sulfides
5.7K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.7K
01:20Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
2.4K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.4K
01:14Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
2.6K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
2.6K
01:11Aryldiazonium Salts to Azo Dyes: Diazo Coupling
3.6K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.6K
01:23Amines to Sulfonamides: The Hinsberg Test
4.3K
The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
Generally, a primary amine reacts with the Hinsberg reagent to produce an N-substituted benzenesulfonamide. The electron-withdrawing sulfonyl...
4.3K